Oct 15, 2025 · 28m · tbpn
Andrew Ross Sorkin on Why 1929 is Happening Again
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Financial journalist Andrew Ross Sorkin explores the striking historical parallels between the 1929 stock market crash and modern speculative markets, while detailing the seven-year investigative research and writing journey behind his new book.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
The hosts as informed peer 3.6 Guest teaching 4.8 Guest disagreement 1.1 The hosts pushing back 1.0
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 10:45 Reframing investment pools vs retail armies
Sorkin directly counters the host's comparison of 1920s investment pools to modern democratized Reddit armies, clarifying that historical market manipulation pools were run strictly by wealthy financial elites.
Hardest push from the hosts ▶ 5:48 Host pushes back on 10x leverage as extremeThe host humorously challenges the notion that 10x leverage in the 1920s was excessive by pointing out that modern crypto markets offer 50x to 100x leverage without hesitation.
Biggest teaching moment ▶ 25:57 Dispelling historical precedent for 1929Sorkin educates the host on financial history, explaining that 1929 market participants could not look back at past crashes because broad-based consumer credit had only been invented ten years prior by General Motors.
The host holds their own ▶ 11:55 Host analyzes incentives of top callersThe host demonstrates strong domain knowledge by citing Keith Raboi's exact 2021 market top prediction and analyzing the asymmetric social incentives of market Cassandras.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Previewing Modern Financial Parallels to the 1920s | 3 | 3 | 1 | 1 | The host opens with light sleep-tracker banter and asks whether Sorkin predicted the current AI bubble. Sorkin clarifies his book was conceived years ago as a character-driven history, though modern parallels like tariffs and meme coins naturally emerged. | |
| Profiling 1920s Titans: Churchill, Mitchell, Glass, and Raskob | 4 | 6 | 1 | 2 | Sorkin provides detailed profiles of 1920s figures including Churchill, Charlie Mitchell, Carter Glass, and John Raskob. The host interjects comparing 1920s 10x margin leverage to modern 100x crypto leverage and connects Raskob's biography to Elon Musk. | |
| Speculation, Excessive Leverage, and Policy Missteps of 1929 | 4 | 6 | 2 | 1 | Sorkin explains the systemic role of leverage, Fed policy inaction, and tariff impacts after 1929. When the host compares historical investment pools to modern Reddit retail armies, Sorkin politely corrects him, noting the original pools were run exclusively by wealthy financial elites. | |
| Market Cassandras, Jesse Livermore, and Timing the Bubble | 4 | 6 | 1 | 1 | The host cites Keith Raboi calling the 2021 market top to ask about historical bubble predictors. Sorkin discusses Roger Babson, Charles Merrill, and Jesse Livermore, emphasizing that being prematurely bearish caused investors to miss 90% upside between 1928 and 1929. | |
| Tariff Policies, Market Euphoria, and Ticker-Tape Information Delays | 4 | 5 | 1 | 1 | The host asks whether policy tools and 'buy the dip' psychology existed in 1929. Sorkin explains Hoover's tariff mandates versus modern bilateral trade authority, and describes how severe ticker-tape delays blinded retail investors during the panic. | |
| Evaluating Retail Investor Signals from Shoeshine Tips to Crypto | 4 | 5 | 1 | 1 | The host questions the validity of shoeshine and taxi driver stock tips as reliable contrarian indicators today. Sorkin shares his research methods, including hiring students to photograph archives during lockdowns and using AI to decipher Fed board diaries. | |
| Writing Craft, Sentence Construction, and Finding the Flow State | 4 | 6 | 2 | 1 | Sorkin outlines his sentence-by-sentence writing discipline and flow state requirements. When the host asks what historical crisis people in 1929 looked back to, Sorkin clarifies they had no real precedent because mass consumer credit was only invented around 1919 by General Motors. | |
| Reflections on Live Media Demands and Concluding Gong Celebration | 2 | 1 | 0 | 0 | The conversation concludes with mutual praise regarding daily live television stamina and content creation, finishing with the show's customary ceremonial gong celebration. |
Statements from this episode (17)
Andrew Ross Sorkin Says Financial Markets Will Not Crash Just Yet
“Yeah it gets, it's a little nerve-wracking, but I don't think we're going off the cliff just yet, I hope.”
Winston Churchill Dined With Wall Street Bankers During 1929 Market Crash
“Churchill happened to be in New York literally the week that the crash was taking place. He'd actually been down on the stock exchange and it was a big dinner that was taking place the night of the crash with every major banker and frankly, every major charact…”
Modern Celebrity CEO Culture Began With Time Magazine Covers In The 1920s
“This was also a period where all of these guys also became celebrities for the first time that happened in the 19 twenties when, you know, time magazine would put these guys on the cover the same way they'd put Babe Ruth and Charles Lindbergh on the cover. So …”
1920s Retail Brokerages Offered 10-to-1 Margin Leverage Without Prospectuses
“These brokerage houses were opening up like Starbucks on the corner of every street, and you could go in, and you put down a dollar. They'd loan you 10 dollars. I mean, like, virtually sight unseen, and there was no prospectuses or anything like, there's no SE…”
Andrew Ross Sorkin Compares 1920s Financier John Raskob To Elon Musk
“John Raskob is Elon Musk. I mean, I got to tell you, John Raskob Created credited General Motors became a amazing investor, then takes all of his winnings, decides to get into politics, a little Elon-like decides to back Al Smith against President Hoover. By t…”
Speculative Investing Is Necessary To Drive Innovations Like Tesla And SpaceX
“You need some speculation in the system. Like, we always say speculation is a dirty word or a bad word, but, you know, the original investors in SpaceX or in Tesla who probably thought the whole thing was insane were speculating. And you need some of that. You…”
Excessive Leverage Is The Primary Accelerant For Systemic Financial Collapses
“Leverage is to me like the match that lights the fire every time when you have too much leverage in the system, that it, that is the problem. You can actually have a lot of crazy things happening. But it's the leverage that really exacerbates it and is the acc…”
The 1930 Smoot-Hawley Tariff Act Caused Global Trade To Drop 60%
“Smoot-Hawley, which was this tariffs, 1930, tariffs happened. Global trade drops by 60% as a result of that.”
The US Stock Market Gained 90% From Early 1928 To September 1929
“The market between the beginning of 28 and September of 29 was up 90%. So if you had not been in the market during that time, you would have not participated in those ups.”
Paul Tudor Jones Believes Current Market Resembles October 1999 Dot-Com Bubble
“I was talking to Paul Tudor Jones about a week ago, and he said, I was asking him this question about bubbles. He said, ah, I think we're in maybe like October, 1999. Right now. And I said, oh, that's interesting. Okay. 99. He said, but there's still, if you s…”
A 1934 Law Gave US Presidents Authority For Bilateral Trade Deals
“One of the ways they tried to fix what happened after Smoot-Hawley was in 1934. They gave the president of the United States the authority, which is what president Trump is using today to make these sort of bilateral deals.”
Brokerage Ticker Tapes Ran Hours Behind During The 1929 Market Crash
“The reason they had all come down there was because when they were up at the brokerages, they couldn't even find out what was happening to their stocks. Cause everything was out of talk about time and technology. They didn't know what You know, the stops on th…”
Social Media Makes Retail Buzz Unreliable As A Market Top Signal Today
“Now with social media, and by the way, all the amazing things you guys are doing, I feel like the exposure, I got fifteen-year-old boys who are twins, and they're so exposed to this stuff, just, and I don't think that they're, because of, I don't think that's …”
Andrew Ross Sorkin Uncovers Previously Unseen 1929 New York Fed Board Minutes
“I got access for the first time to the Federal Reserve Board minutes from 29 in New York. They'd never been made public, so that really created sort of like an undergirding.”
Banker Charlie Mitchell Took Personal Loans To Cover 1929 Share Buybacks
“The guy, Charlie Mitchell, that I told you about before, his bank almost goes under because the bank bought, the bank was trying to buy back its own shares during all this, and it bought back too many, and couldn't afford to buy them. And so, he didn't want an…”
Trader Jesse Livermore Stationed Private Informants On The 1929 Exchange Floor
“And then Jesse Livermore, this trader I was telling you about, because he didn't Because he was so worried about the issue of having bad information. He paid for his own people to be on the floor. So then they would call him. It was like Citadel placing, you k…”
General Motors Auto Loans Normalized American Consumer Debt In 1919
“It wasn't till 1919 that people were even started to think about taking on debt or anything like that in the country to then go trade. It was really a function of General Motors, by the way. General Motors started loaning money to people to buy cars. That was,…”